WO2016102316A1 - Process for increasing the stability of a composition comprising polyunsaturated omega-6 fatty acids - Google Patents

Process for increasing the stability of a composition comprising polyunsaturated omega-6 fatty acids Download PDF

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Publication number
WO2016102316A1
WO2016102316A1 PCT/EP2015/080293 EP2015080293W WO2016102316A1 WO 2016102316 A1 WO2016102316 A1 WO 2016102316A1 EP 2015080293 W EP2015080293 W EP 2015080293W WO 2016102316 A1 WO2016102316 A1 WO 2016102316A1
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Prior art keywords
composition
lysine
fatty acids
polyunsaturated omega
acid
Prior art date
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PCT/EP2015/080293
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English (en)
French (fr)
Inventor
Günter Knaup
Milan Latinovic
Michael Schwarm
Original Assignee
Evonik Degussa Gmbh
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=52344990&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2016102316(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to CN201580070558.XA priority Critical patent/CN107105693B/zh
Priority to EP15820481.8A priority patent/EP3236783B1/en
Priority to PL15820481T priority patent/PL3236783T3/pl
Priority to ES15820481T priority patent/ES2776393T3/es
Priority to BR112017013445-4A priority patent/BR112017013445B1/pt
Priority to MX2017008274A priority patent/MX2017008274A/es
Priority to KR1020177016895A priority patent/KR20170094789A/ko
Priority to US15/538,719 priority patent/US20170367394A1/en
Priority to RU2017125963A priority patent/RU2706072C2/ru
Application filed by Evonik Degussa Gmbh filed Critical Evonik Degussa Gmbh
Priority to JP2017533761A priority patent/JP6714000B2/ja
Priority to SG11201704399RA priority patent/SG11201704399RA/en
Priority to CA2969157A priority patent/CA2969157C/en
Priority to MYPI2017702257A priority patent/MY190506A/en
Priority to AU2015371457A priority patent/AU2015371457B2/en
Priority to DK15820481.8T priority patent/DK3236783T3/da
Priority to NZ732380A priority patent/NZ732380A/en
Publication of WO2016102316A1 publication Critical patent/WO2016102316A1/en
Priority to IL252482A priority patent/IL252482B/en
Priority to CONC2017/0005849A priority patent/CO2017005849A2/es
Priority to PH12017501144A priority patent/PH12017501144A1/en
Priority to ZA2017/04821A priority patent/ZA201704821B/en

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/1882—Polyunsaturated fatty acids

Definitions

  • Oxidation has negative, both nutritional and organoleptic, consequences; namely, changes in nutritional value such as the destruction of essential fatty acids; rancidity which produces off-flavors and pronounced odors; color changes such as darkening of fats and oils, as well as flavor loss. Oxidation of PUFAs produces a complex mixture of volatile secondary oxidation products, and these cause particularly objectionable off-flavors.
  • compositions comprising polyunsaturated omega-6 fatty acids can be stabilized against oxidation by a process comprising the following steps: (i) providing a starting composition comprising at least one polyunsaturated omega-6 fatty acid component;
  • PUFA is used interchangeably with the term polyunsaturated fatty acid and defined as follows: Fatty acids are classified based on the length and saturation characteristics of the carbon chain. Short chain fatty acids have 2 to about 6 carbons and are typically saturated. Medium chain fatty acids have from about 6 to about 14 carbons and are also typically saturated. Long chain fatty acids have from 16 to 24 or more carbons and may be saturated or unsaturated. In longer chain fatty acids there may be one or more points of unsaturation, giving rise to the terms "monounsaturated” and "polyunsaturated,” respectively. In the context of the present invention long chain polyunsaturated fatty acids having 20 or more carbon atoms are designated as polyunsaturated fatty acids or PUFAs.
  • PUFAs are categorized according to the number and position of double bonds in the fatty acids according to well established nomenclature. There are two main series or families of LC-PUFAs, depending on the position of the double bond closest to the methyl end of the fatty acid: The omega-3 series contains a double bond at the third carbon, while the omega-6 series has no double bond until the sixth carbon. Thus, docosahexaenoic acid (“DHA”) has a chain length of 22 carbons with 6 double bonds beginning with the third carbon from the methyl end and is designated “22:6 n-3" (all-cis-4,7,10,13,16, 19-docosahexaenoic acid).
  • DHA docosahexaenoic acid
  • omega-3 PUFA Another important omega-3 PUFA is eicosapentaenoic acid ("EPA”) which is designated “20:5 n-3” (all-cis-5,8, 1 1 , 14, 17- eicosapentaenoic acid).
  • An important omega-6 PUFA is arachidonic acid ("ARA") which is designated “20:4 n-6” (all-cis-5,8, 1 1 , 14-eicosatetraenoic acid).
  • ARA arachidonic acid
  • Other omega-3 PUFAs include:
  • ETE Eicosatrienoic acid
  • ETA Eicosatetraenoic acid
  • HPA Heneicosapentaenoic acid
  • DPA Docosapentaenoic acid
  • DPA Docosapentaenoic acid
  • DPA Docosapentaenoic acid
  • DPA Docosapentaenoic acid
  • DPA Docosapentaenoic acid
  • DPA Tetracosapentaenoic acid 24:5 (n- 3) (all-cis-9, 12, 15, 18,21-tetracosapentaenoic acid), Tetracosahexaenoic acid
  • suitable source materials include animal-derived products such as eggs, but in particular, material derived from microbial, especially fungal and/or algal fermentation. Typically, such material further contains substantial amounts of other naturally occurring fatty acids.
  • Typical methods of processing such source materials may include steps for obtaining crude oils such as extraction and separation of the source material, as well as steps for refining crude oils such as settling and degumming, de-acidification, bleaching, and deodorization, and further steps for producing omega-6 PUFA-concentrates from refined oils such as de-acidification, trans- esterification, concentration, and deodorization (cf. e.g. EFSA Scientific Opinion on Fish oil for Human Consumption).
  • Any processing of source materials may further include steps for at least partially transforming omega-6 PUFA-esters into the corresponding free omega-6 PUFAs or inorganic salts thereof.
  • a decrease of the degree of oxidation resulting from exposure to oxidizing conditions indicates a very high level of stability towards oxidation which should be interpreted as being even higher than the level of stability of a sample yielding an unchanged degree of oxidation as a result of exposing the sample to comparable oxidizing conditions.
  • measures are known in the art for quantifying the degree of oxidation of a sample. In the broadest sense of the present invention, any of these measures can be used. In preferred embodiments of the present invention one or more of the following measures are used for quantifying the degree of oxidation: Peroxide Value (PV), Anisidine Value (AV), Totox Value.
  • step 8 If the starting color of the solution is deep red orange, titrate slowly with mixing until the color lightens. If the solution is initially a light amber color, go to step 9. 9. Using a dispensing device, add 1 ml of starch solution as indicator.
  • An exemplary procedure for determining the Anisidine Value (AV) of a sample is performed as follows:
  • the anisidine value is defined as 100 times the optical density measured in a 1 cm cell of a solution containing 1 g of the substance to be examined in 100 ml of a mixture of solvents and reagents according to the following method. Carry out the operations as rapidly as possible, avoiding exposure to actinic light.
  • A1 absorbance of test solution (b) at 350 nm
  • A2 absorbance of test solution (a) at 350 nm
  • m mass of the substance to be examined in test solution (a), in grams.
  • the degree of oxidation in steps (1 ) and (3) is assessed by determining Peroxide Value (PV) and/or Anisidine Value (AV); further, preferably, the oxidizing conditions in step (2) are selected from one of the following: storage in open containers exposed to air at room temperature over a defined period of time of at least ten days; storage in open containers exposed to air at 50 °C over a defined period of time of at least three days.
  • PV Peroxide Value
  • AV Anisidine Value
  • polyunsaturated omega-6 fatty acid component may be any compositions containing substantial amounts of at least one polyunsaturated omega-6 fatty acid component, wherein each type (i.e. molecular species) of free omega-6 PUFA (with "free” indicating the presence of a free carboxylic acid function) constitutes a different polyunsaturated omega-6 fatty acid component.
  • Such compositions may further comprise other naturally occurring fatty acids in free form.
  • such compositions may further comprise constituents that by themselves are solid, liquid or gaseous at room temperature and standard atmospheric pressure.
  • Corresponding liquid constituents include constituents that can easily be removed by evaporation and could thus be considered as volatile constituents as well as constituents that are difficult to remove by evaporation and could thus be considered as non-volatile constituents.
  • gaseous constituents are considered as volatile constituents.
  • Typical volatile constituents are water, alcohols and supercritical carbon dioxide.
  • starting compositions without taking account for volatile constituents, have a PUFA-content PC (i.e. the total content of one or more free polyunsaturated omega-6 fatty acids) of at least 75 wt%, up to 25 wt% of other naturally occurring fatty acids in free form, and up to 5 wt% of other constituents that by themselves are solid or liquid at room temperature and standard atmospheric pressure.
  • PUFA-content PC i.e. the total content of one or more free polyunsaturated omega-6 fatty acids
  • the lysine composition provided in step (ii) of the process of the present invention is a composition comprising substantial amounts of free Lysine (Lys).
  • the lysine composition may further comprise constituents that by themselves are solid, liquid or gaseous at room temperature and standard atmospheric pressure.
  • Corresponding liquid constituents include constituents that can easily be removed by evaporation and could thus be considered as volatile constituents as well as constituents that are difficult to remove by evaporation and could thus be considered as nonvolatile constituents.
  • gaseous constituents are considered as volatile constituents. Typical volatile constituents are water, alcohols and supercritical carbon dioxide.
  • starting compositions contain mostly free PUFAs and other naturally occurring fatty acids in free form and lysine compositions contain mostly free lysine, thus yielding product compositions mostly consisting of salts of lysine with PUFAs and other naturally occurring fatty acids.
  • step (iii) of the process of the present invention starting composition and lysine composition are combined.
  • Combining can be achieved by any means allowing formation of a product composition comprising at least one salt of a cation derived from lysine with an anion derived from a polyunsaturated omega-6 fatty acid.
  • a typical way of combining starting composition and lysine composition would be admixing aqueous, aqueous-alcoholic or alcoholic solutions of each and removing the solvent subsequently.
  • a preferred way of combining starting composition and lysine composition is admixing aqueous, aqueous-alcoholic or alcoholic solutions of each and removing the solvent subsequently.
  • a cation derived from lysine is a cation obtained by protonation of lysine.
  • the product composition contains no substantial amounts of antioxidants, wherein no substantial amounts means that the product composition contains less than 5 wt%, 3 wt%, 1 wt%, or 0.1 wt% of antioxidants and wherein the antioxidants are selected from vitamin C and esters thereof, erythorbic acid and esters thereof, vitamin E and esters thereof, polyphenols and esters thereof, carotinoids, gallates and esters thereof, butylated hydroxyanisole and esters thereof, butylated hydroxytoluene and esters thereof, rosemary oil, hexylresorcinol and esters thereof.
  • the product composition contains no antioxidants at all, wherein the antioxidants are selected from vitamin C and esters thereof, erythorbic acid and esters thereof, vitamin E and esters thereof, polyphenols and esters thereof, carotinoids, gallates and esters thereof, butylated hydroxyanisole and esters thereof, butylated hydroxytoluene and esters thereof, rosemary oil, hexylresorcinol and esters thereof.
  • the antioxidants are selected from vitamin C and esters thereof, erythorbic acid and esters thereof, vitamin E and esters thereof, polyphenols and esters thereof, carotinoids, gallates and esters thereof, butylated hydroxyanisole and esters thereof, butylated hydroxytoluene and esters thereof, rosemary oil, hexylresorcinol and esters thereof.
  • the product composition exhibits higher stability towards oxidation than the starting composition.
  • at least one measure describing the stability of a composition towards oxidation e.g. at least one measure as described above, indicates a higher stability towards oxidation for the product composition than for the starting composition.
  • the amount of carboxylic acid functions n(ca) in the starting composition provided in step (i) can be determined by standard analytical procedures well known in the art, e.g. acid base titration.
  • the starting composition provided in step (i) does not contain substantial amounts of fatty acid esters, thus yielding a product composition devoid of substantial amounts of fatty acid esters as well. Accordingly, in preferred embodiments of the present invention the starting composition provided in step (i) does not contain more than x(fe) wt% of fatty acid esters, thus yielding a product composition comprising a maximum of x(fe) wt% of fatty acid esters, wherein x(fe) is selected from 5, 3, 1 , 0.3, 0. In particularly preferred embodiments x(fe) is 1.
  • salts of lysine with omega-6 PUFAs can in fact be obtained via spray drying in a facile manner.
  • Conditions for spray drying always, have to be adapted to the particular spray-drying equipment used. However, it is well within the scope of routine laboratory work of a person of skill in the art to perform such adaption in the present case.
  • the solvent of the admixture subjected to spray drying conditions is an aqueous-alcoholic solvent system containing 20 wt% to 90 wt% water and 80 wt% to 10 wt% alcoholic solvents.
  • the solvent content of the solid product composition will vary depending on spray drying conditions and substrates used, however, it was presently found that even at very low solvent contents in the solid product composition oxidative damage does not occur. As outlined further above, this could not have been expected.
  • a solid product composition with a low solvent content is obtained.
  • aqueous, aqueous-alcoholic or alcoholic solutions of starting composition and lysine composition are first admixed, and subjected to spray drying conditions subsequently, thus yielding a solid product composition comprising at least one salt of a cation derived from lysine with an anion derived from a polyunsaturated omega-6 fatty acid, with a solvent content SC selected from the following: SC ⁇ 5 wt%, SC ⁇ 3 wt%, SC ⁇ 1 wt%, SC ⁇ 0.5 wt%.
  • SC is selected as SC ⁇ 1 wt%.
  • the present invention further, comprises compositions obtainable by any of the processes of the invention.
  • food products comprise but are not limited to baked goods, vitamin supplements, diet supplements, powdered drinks, doughs, batters, baked food items including e.g. cakes, cheesecakes, pies, cupcakes, cookies, bars, breads, rolls, biscuits, muffins, pastries, scones, and croutons; liquid food products e.g.
  • the present invention further, comprises use of compositions, obtainable by any of the processes of the invention, for the manufacture of nutritional products comprising polyunsaturated omega-6 fatty acids.
  • nutritional products comprise any type of nutraceutical, nutrient or dietary supplement, e.g. for supplementing vitamins, minerals, fiber, fatty acids, or amino acids.
  • the present invention further, comprises use of compositions, obtainable by any of the processes of the invention, for the manufacture of pharmaceutical products comprising polyunsaturated omega-6 fatty acids.
  • Oligomeric PUFA constituents as well as their derivatives were quantified by gel-chromatographic means (GPC, styroldivinylbenzene-phase with tetrahydrofuran containing trifluoroacetic acid used as eluent).
  • GPC gel-chromatographic means
  • Rl refractive index
  • Ethanol content was determined by 1-H-NMR spectroscopy.
  • Phases were separated after 10 min of subsequent stirring and the product phase was washed with 3 time 125 ml water each and then 125 ml aqueous sodium sulfate solution 10-wt-%.
  • 500 g gamma-linolenic acid was obtained as an oil with an Anisidine Value of 7.6 A/g and a Peroxide Value of 5.6 mmol/kg. .
  • Oligomer content was determined as 0.3 area-% (gel-chromatography, Rl-detector).

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JP2017533761A JP6714000B2 (ja) 2014-12-23 2015-12-17 ω−６系多価不飽和脂肪酸を含む組成物の安定性を向上させる方法
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BR112017013445-4A BR112017013445B1 (pt) 2014-12-23 2015-12-17 Processo para aumentar a estabilidade de uma composição que compreende ácidos graxos ômega 6 poli-insaturados e uso da composição de produto
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KR1020177016895A KR20170094789A (ko) 2014-12-23 2015-12-17 다중불포화 오메가-6 지방산을 포함하는 조성물의 안정성을 증가시키는 방법
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WO2021023849A1 (en) 2019-08-08 2021-02-11 Evonik Operations Gmbh Down streaming process for the production of polyunsaturated fatty acid salts
WO2021023857A1 (en) 2019-08-08 2021-02-11 Evonik Operations Gmbh Solubility enhancement of poorly soluble actives
WO2021023848A1 (en) 2019-08-08 2021-02-11 Evonik Operations Gmbh Method of preparing a solid dosage form and a lubricant
WO2021023850A1 (en) 2019-08-08 2021-02-11 Evonik Operations Gmbh Method of preparing a solid dosage form and a binder
EP3804699A1 (en) 2019-10-10 2021-04-14 Evonik Operations GmbH Method of preparing a solid dosage form and a binder
CN115298293A (zh) * 2020-01-30 2022-11-04 硅循环股份有限公司 多不饱和脂肪酸的碱性氨基酸盐的固体形式的制备方法
WO2021151199A1 (en) * 2020-01-30 2021-08-05 Silicycle Inc. Process for preparing a solid form of basic amino acid salts of polyunsaturated fatty acids
WO2021197969A1 (en) 2020-04-01 2021-10-07 Evonik Operations Gmbh Preparation for use as vasorelaxant
WO2021197971A1 (en) 2020-04-01 2021-10-07 Evonik Operations Gmbh Preparation for use as antioxidant

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